


Dare Of All Dares

by abiotic_butterfly



Series: A Depressing Side [9]
Category: Supernatural
Genre: Anal bleeding, Angst, Dare sex, Dumpster Fucking, F/M, Gay Castiel, Homophobia, M/M, Rough Sex, Straight Dean, Suicide, Unrequited Love, anal fucking, dares, filming without permission, jumping, unwanted sex
Language: English
Status: Completed
Published: 2018-11-08
Updated: 2018-11-08
Packaged: 2019-08-20 12:51:52
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death, Rape/Non-Con, Underage
Chapters: 1
Words: 1,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16556090
Author URL: https://archiveofourown.org/users/abiotic_butterfly/pseuds/abiotic_butterfly
Summary: When Dean is dared by his friends to have sex with the schools geek Castiel things are taken too far.





	Dare Of All Dares

Castiel was walking to his locker when he was pushed against the bright red lockers by the hottest guy in his school. 

“Dean?” He breathed out, his eyes widening behind his glasses. 

“Hey Cas.” His voice was husky and deep and Castiel was sure he was shivering in his khakis and sweater vest.

“Look, I was thinkin’ you and me get outa here.” His eyes looked over his shoulder with a worried and annoyed expression, but that was completely gone when he looked back to Castiel, only his signature smirk and his glinting eyes could be seen. 

“O-Oh okay.” He breathed out nervously, his heart fluttering and his stomach turning as he continued to make eye contact with the guy he’d had a crush on for over ten years.

Dean grabbed onto his arm with that, completely dragging the smaller boy away from his locker and out of the school. 

“We’re leaving school? That’s against the rules, we can’t.” He tried to argue but really it wasn’t long lived because Dean fucking Winchester was pulling him out of school and behind the dumpsters in the back.

Dean didn’t wait for anything, he yanked off his flannel over shirt and then his black t-shirt. “Gonna stand there? Take off yours.” He looked at Castiel expectantly. 

The black haired boy nodded frantically, the book he was clutching in his hand dropped to the ground and yanked off his vest and buttoned up shirt, leaving the two boys shirtless.

Cas looked at Dean, waiting for what the older boy would say to do next. The popular boy unzipped his pants and pushed his underwear aside so that his cock sprung free. “Take off the rest.” Cas nodded immediately, hurrying to comply. 

Cas couldn’t help but look at Dean’s package. It was impression, but it wasn’t fully hard, unlike Cas’s now straining dick. “Want me to- to you know?” He looked innocently up at Dean and then to the ground.

Dean hesitated, “yeah, um, sure whatever.”

Cas nodded, nervously turning and lowering to his knees. The asphalt hurt and he knew that after too long he’d have imprints and blood to deal with later. But right now that was not the least bit important.

He delicately laid his hand on Dean’s hip and tentatively sucked the other boy’s cock into his mouth. 

He heard a moan and found himself smiling, he was the reason the most popular boy in school was pleasured. His blue eyes looked up, hoping to see green staring back. 

But Dean wasn’t looking at him, his head was leaned back and he was staring at the sky. Cas’s brows furrowed and he felt his stomach flip in an uncomfortable way. 

He picked up his pace, going up and down faster than before, sucking and licking at the head of Dean’s dick. Nothing. Not once did he look down at the other boy.

Cas was the one to look down, his vision being met with the taller boys muscular abs. 

A hand suddenly grabbed his hair and he was yanked back, his mouth opening in surprise. “Wh-“ he coughed out, his voice rough and abnormal. 

“I’m ready.” Dean nodded for Cas to stand up so that’s what he did. “Turn around.” He used his finger to make a circular motion. 

Slowly and cautiously Castiel turned around, waiting nervously for Dean to give him his next command. 

“Wall.” 

Cas walked forward, all the way to the dumpster brick wall that Dean had ordered him to go to. 

The other boy grabbed his hips and pushed him down, moving his body in an uncomfortable and weird position.

His breath caught in his throat when he felt something push against his rim. He whimpered a bit at the intrusion because it was too much alll at once and he felt like he was being torn apart.

“Fuck- ah!” He cried out, tears filling his eyes, his nails digging into the brick wall. 

Dean’s cock pushed the rest of the way inside Cas’s body, the smaller boy shaking and stuttering in pain. “Dean…” he whispered out helplessly.

He felt the other boys dick pull out slowly, the object lodged in him gliding against his walls. Then the pain was back in full force, a hardcore pounding that Castiel had never endured before. “Dean- Dean- Dean- ah~ ah! Ha- ahh!” He was alternating between cries and moans, hoping that it would get better like everyone had said it would. 

He swore he could feel blood trickling down his legs but that didn’t matter, Dean had hit that spot. The most wonderful and amazing spot in his whole body. If only he could touch his cock, but moving even an inch would alter the position his body was in and he’d get crushed by Dean’s weight. 

“Dean~ ah~ please- harder- I need it harder-“ He was cut off my his own moan, loud and full of passion, something that surprised himself. 

Dean’s thrusts became rougher, a constant pounding that would snap the youngest ones body every second. “De- ah! Dean~” He keened out.

“Can’t fucking-“ Dean huffed behind him, his pace slowing and his thrusts decreasing.

Cas looked around worriedly, he wasn’t sure that was supposed to happen. He squeezed his hole around the other boys cock, finding that it was…losing its hardness.

“Dean?” He whimpered out, his heart thumping against his chest, his ribs burning in pain. The jock hadn’t come, there was no reason he should have stopped. “Are you okay-“

Dean slammed him against the wall, a hand coming up to cover his mouth. 

Cas jerked at the motion, his moans vibrating from the hand keeping them silent. His heart throbbed and he body scraped and smacked into the brick. 

He tried to wrap his hands around Dean’s, not liking him being kept from using his voice.

Dean’s jeans were pushing into his skin more forcefully and he could feel tears pricking and leaving his eyes. 

Dean’s hand moved from where it was bruising his hip, his movements faltered a bit and he couldn’t tell what was going on anymore. A soft click could be heard behind Cas and his eyes widened.

What the hell was that? It couldn’t be a gun, could it?! No they didn’t sound like that.

He tried to turn his head but the hand on his mouth forced him to stay still.

He wrapped his right arm around Dean’s and yanked, between Dean’s inconsistent trusts and Cas’s curiosity the smaller boy managed to get out of Dean’s hold.

When he turned around he was horrified, his eyes widened and his heart fell into his stomach. His lip quivering and his body shaking at the realization. 

Dean was standing there dumbfounded, phone in hand while he tried to put his dick back inside his underwear.

“You were recording me?” Cas whispered out. 

Dean looked down, a dark blush covering his cheeks that made his freckles stand out.

“It was a dare…”

Tears filled Cas’s eyes and he found himself physically sick. “A dare? A dare to fuck the school loser?!” Tears poured out of his eyes and he was openingly sobbing.

Dean didn’t respond, “I thought you’d say no. I’m not gay Cas, or bi, in case you couldn’t tell. Figured you wouldn’t believe me.”

Cas cried more, the implication of ‘thought you weren’t that dumb’ hung between them. “I hope it was worth it!” He cried out, his body going stiff with pain when he tried to walk. He refused to hiss or cry though, he wouldn’t do that in front of Dean. 

So he bit his lip and pulled up his underwear and pants, walking as best as he could over to where he’d dropped his shirt and vest in a hurry to get them off. 

He limped off sadly, his heart broken and his body aching. 

Cas had cried himself to sleep that night, images Dean using him haunting his mind. 

When he got to school the next day, it was the most horrendous day of his life, it seemed like he never woke up from his horrific dream.

The school hallways were filled with the picture. The one of Dean fucking him. 

The caption “Dean The Daredevil” on all of them. And even though it didn’t show his face, only the part where Cas’s ass was being impaled by Dean’s cock, everyone knew it was him.

Dean’s friends must have spread it around.

He had gotten pushed into lockers every chance someone got, the popular girls, who were all friends with Dean’s girlfriend Lisa spread every hurtful or illmanorded message about him as possible. And the jocks…they were the worst. 

“You like it in the ass, Cas?!” 

“How about I fuck you in the bathroom later, promise you’ll moan like ya did for Dean!”

“Looked like you enjoyed yourself there!”

One of them even cornered him in the bathroom and ripped off his vest and started unbuttoning his shirt. 

Castiel almost had a heart attack then, but apparently the guys intention was never to fuck him. It was to get halfway done with his shirt and force Castiel to stay still for another picture that would be going around the school in a matter of seconds. 

By the end of the day he couldn’t take it. He didn’t want to be remembered as the kid that took their life because of a stupid joke. But it looked like that’s what was going to happen.

He tried remembering his family, people that cared about him. But then Dean bending him over would overpower it, kids in the library laughing over the short video Dean had taken of him being fucked, his moans being heard even past the cover of Dean’s hand. 

He climbed to the roof of the school, seemed like a right place to end it all. Right near where Dean fucked him, maybe his body would fall and crush the dumpster, they could just leave him there.

His phone dropped before he did, his phone had always been lonely and boring social media with 5 - 10 followers were filled with hate comments about how he was a whore that deserved to get fucked by anyone who willingly wanted to use his body. 

He stepped onto the ledge, a shiver going through his body. Ugh, he body. No longer was he pure, he’d given his virginity away so easily. No prompting necessary just ‘okay Dean, whatever you say Dean.’ Maybe he really was a slut.

He leaned forward, his body wanting to throw up what little it had left. Just the thought of remaining in this used up and pointless flesh suit made him hurl. Or maybe it was everything else.

Tears slid down his face and he sobbed openly. 

He heard shouts from below him and looked to see a crowd of people filing in. 

Were they real? 

Was he going insane?!

“Do it faggot!”

“Fuckin’ jump, pussy!”

“Do it ya whore!”

“Dean.” Cas’s voice cracked and his vision blurred, it didn’t matter if they were real or not. He leaned forward more, his body losing balance and falling, faster, and faster, the darkness that followed was the best feeling he’d ever had in his lifetime.


End file.
